Alkaline hydrolysis

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Alkaline hydrolysis, in organic chemistry, usually refers to types of nucleophilic substitution reactions in which the attacking nucleophile is a hydroxide ion.

Example[edit]

In the alkaline hydrolysis of esters and amides the hydroxide ion nucelophile attacks the carbonyl carbon in a nucleophilic acyl substitution reaction. This mechanism is supported by isotope labeling experiments. For example, when ethyl propionate with an oxygen-18 labeled ethoxy group is treated with sodium hydroxide (NaOH), the oxygen-18 is completely absent from the sodium propionate product and is found exclusively in the ethanol formed.[1]

Reacting isotopically labeled ethyl propionate with sodium hydroxide proves the proposed mechanism for nucleophilic acyl substitution.

Uses[edit]

Drain cleaners take advantage of this method to dissolve hair and fat in pipes.

See also[edit]

References[edit]

  1. ^ McMurry, John (1996). Organic Chemistry (4th ed.). Pacifc Grove, CA: Brooks/Cole Publishing Company. pp. 820–821. ISBN 0534238327.